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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-09-22 21:06:30 UTC
HMDB IDHMDB00759
Secondary Accession NumbersNone
Metabolite Identification
Common NameGlycyl-L-leucine
DescriptionGlycyl-l-leucine is a dipeptide that appears to be a common substrate for glycyl-leucine dipeptidase. It belongs to the family of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Structure
Thumb
Synonyms
ValueSource
G-LChEBI
GLChEBI
Gly-L-leuChEBI
Glycyl-L-leucineChEBI
GlycylleucineChEBI
(2S)-2-[(2-Aminoacetyl)amino]-4-methylpentanoateGenerator
Glycyl-leucineHMDB
N-Glycyl-L-leucineHMDB
Chemical FormulaC8H16N2O3
Average Molecular Weight188.2242
Monoisotopic Molecular Weight188.116092388
IUPAC Name(2S)-2-(2-aminoacetamido)-4-methylpentanoic acid
Traditional Nameglycyl-L-leucine
CAS Registry Number869-19-2
SMILES
CC(C)C[C@H](NC(=O)CN)C(O)=O
InChI Identifier
InChI=1S/C8H16N2O3/c1-5(2)3-6(8(12)13)10-7(11)4-9/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t6-/m0/s1
InChI KeyInChIKey=DKEXFJVMVGETOO-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point233 - 235 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.2 mg/mLALOGPS
logP-2.1ALOGPS
logP-2.7ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)8.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity46.97 m3·mol-1ChemAxon
Polarizability19.4 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0016-1900000000-a852c69819cf24f4e741View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-b162700f9bcc75357713View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9000000000-5cd918e7e11bfce7be57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-541d9e8d735cd6e426ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001u-0900000000-5bca6608db38d3ad7553View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-3900000000-8b68a3411c22d0adc0b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00e9-9500000000-6e99a1c2936e770f9424View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-9000000000-9271b05afa978548360dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-0900000000-727fca50027e24ece915View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0019-9800000000-955d0cb4dc730f98f2b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-9000000000-dc63ae2d4fc2193e80f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-9000000000-eab8ffe1748c1c1c95a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000f-9100000000-c6da64dfa236dbcb2575View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Small Intestine
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedBoth
Normal
details
SalivaDetected and Quantified0.00296 +/- 0.0145 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified0.918 +/- 1.35 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.07 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022228
KNApSAcK IDNot Available
Chemspider ID83812
KEGG Compound IDC02155
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkL-leucine
NuGOwiki LinkHMDB00759
Metagene LinkHMDB00759
METLIN ID5727
PubChem Compound92843
PDB IDNot Available
ChEBI ID185298
References
Synthesis ReferenceBolster J M; Vaalburg W; Elsinga P H; Woldring M G; Wynberg H Synthesis of carbon-11 labelled glycine and the dipeptides L-phenylalanylglycine and L-leucylglycine. International journal of radiation applications and instrumentation. Part A, Applied radiation and isotopes (1986), 37(9), 985-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thompson JA, Markey SP, Fennessey PV: Gas-chromatographic/mass-spectrometric identification and quantitation of tetronic and deoxytetronic acids in urine from normal adults and neonates. Clin Chem. 1975 Dec;21(13):1892-8. [1192581 ]
  2. Smirnov KV, Syrykh GD, Legen'kov VI, Goland-Ruvinova LG, Medkova IL: [Digestive system status after prolonged space flights] Kosm Biol Aviakosm Med. 1982 Mar-Apr;16(2):19-22. [7070032 ]